N-hydrocarbyl amines can be prepared by known methods through the reaction of a hydrocarbon monochloride and a nitrogen-containing compound having at least one hydrogen atom on a nitrogen atom. The problem encountered in that preparative route is the obtension of a reactive hydrocarbon monochloride when the desired N-hydrocarbyl substituent is to be derived from a mono-alkene hydrocarbon having a terminal double bond. Direct chlorination of such an alkene hydrocarbon with liquid or gaseous chlorine results in random chain chlorination, chlorination of side chains and the formation of products containing the relatively unreactive neopentyl chloride. Such a product is relatively unreactive with HN&lt; containing compounds. Chlorination of ethylenic compounds with peroxidecatalyzed sulfuryl chloride (SO.sub.2 Cl.sub.2) is described by M. S. Kharasch and H. C. Brown in J.A.C.S. 61, 3432-34. For example there is described such chlorination of cyclohexene to dichlorocyclohexane, allyl chloride to 1,2,3-trichloro propane, sym. dichloroethylene to sym. tetrachloroethane, stilbene to d,d' and .beta.,.beta.'-stilbene dichlorides and tetrapenylethylene to its dichloride. In each instance that chlorination of ethylenic compound added chlorines to both sides of the double bond and produce a saturated compound. The authors in that and prior articles point out that such sulfuryl chloride reaction of ethylenic compounds not peroxide-catalyzed is either so slow as to be not feasible for even laboratory use or does not proceed at all.
Chlorination with liquid or gaseous chlorine of alkenes having a terminal double bond or an internal double bond can be readily conducted to high chlorine contents. For example, a polybutene of average molecular weight of about 2000 can be so chlorinated to a 35% chlorine content. But the resulting chlorinated alkene is relatively unreactive with such HN&lt; group nitrogen-containing compounds or even alkali metal hydroxides because most of the chlorine atom substituents are rather stably bound.
N-hydrocarbyl derivatives of aliphatic polyamines having hydrocarbyl-substituents of from about 700 to about 100,000 in molecular weight (50-7145 carbon atoms) are described in U.S. Pat. No. 3,275,554 as non-ash forming detergent addition agents for mineral lubricant oils.